Back HomeLewisboro, N.Y.
Lewisboro includes the hamlets of South Salem, Cross River, Goldens Bridge, Waccabuc, Vista and Lewisboro. This rural area has been gifted with an abundance of water. Enchanting lake homes are numerous around Truesdale Lake, Lake Waccabuc, Lake Katonah, Lake Kitchawan and the twin lakes of Oscaleta and Rippowam. Swimming, canoeing, sailing and fishing are among the activities available to lakeside residents.
Lewisboro has many facets. The southeast section borders the town of Pound Ridge and echoes that landscape with rugged rock outcroppings and varied topography. Bedford lies along the southwestern boundary and North Salem is on the north side, so Lewisboro is close to horse country. The eastern side borders Fairfield County, CT.
Many of Westchester’s antique, revolutionary houses are tucked away throughout Lewisboro. A large part of the Pound Ridge Reservation lies in Lewisboro, providing access to 4,700 acres of hiking, camping and cross-country skiing. The renowned John Jay School system serves Lewisboro.
ACTIVE LISTINGS:
$520,000
Pending
2 Woodway Road South Salem, New York
4 Beds 3 Baths 2,037 SqFt 2 Acres
$2,000,000
Active
33 Truesdale Lake Drive South Salem, New York
2 Beds 4 Baths 3,778 SqFt 0.574 Acres
$1,795,000
Active
121 Post Office Road South Salem, New York
3 Beds 2 Baths 3,307 SqFt 5.61 Acres
$1,481,000
Active
1 Canaan Circle South Salem, New York
4 Beds 5 Baths 4,078 SqFt 2.32 Acres
$1,450,000
Pending
22 Bouton Street South Salem, New York
3 Beds 4 Baths 3,528 SqFt 0.6 Acres
$1,395,000
Pending
1090 Route 35 South Salem, New York
5 Beds 5 Baths 3,815 SqFt 17.16 Acres
$1,275,000
Active
29 Oscaleta Road South Salem, New York
3 Beds 2 Baths 2,076 SqFt 3.78 Acres
$1,229,900
Pending
40 Gilbert Street South Salem, New York
3 Beds 4 Baths 2,161 SqFt 0.305 Acres
$1,199,000
Active
8 Roads End Road South Salem, New York
3 Beds 3 Baths 3,781 SqFt 2.19 Acres
$1,199,000
Pending
3 Scenic Drive South Salem, New York
4 Beds 4 Baths 3,079 SqFt 1.1 Acres
$1,150,000
Active
1 Lakeview Road South Salem, New York
2 Beds 3 Baths 2,386 SqFt 0.765 Acres
$1,100,000
Active
31 Tri Brook Drive South Salem, New York
4 Beds 4 Baths 2,556 SqFt 2.03 Acres
$1,100,000
Pending
35 Boutonville Road South Salem, New York
3 Beds 3 Baths 2,622 SqFt 5.86 Acres
$1,100,000
Active
1196 Route 35 South Salem, New York
5 Beds 5 Baths 3,648 SqFt 5.33 Acres
$1,099,000
Pending
94 Bouton Road South Salem, New York
4 Beds 3 Baths 2,623 SqFt 1.32 Acres
$1,095,000
Active
13 Laurie Lane South Salem, New York
3 Beds 3 Baths 3,200 SqFt 5 Acres
$1,050,000
Active
7 Main Street South Salem, New York
3 Beds 3 Baths 2,116 SqFt 0.59 Acres
$999,995
Pending
30 Benedict Road South Salem, New York
3 Beds 2 Baths 2,400 SqFt 3.21 Acres
$975,000
Pending
26 Tri Brook Drive South Salem, New York
4 Beds 3 Baths 3,016 SqFt 2 Acres
$950,000
Pending
5 Canaan Circle South Salem, New York
4 Beds 3 Baths 2,246 SqFt 2.09 Acres
$949,000
Pending
123 East Street South Salem, New York
4 Beds 4 Baths 2,950 SqFt 5.6 Acres
$949,000
Pending
16 Gilbert Street South Salem, New York
4 Beds 2 Baths 1,396 SqFt 0.35 Acres
$895,000
Active
10 Silvermine Drive South Salem, New York
4 Beds 3 Baths 2,650 SqFt 1.73 Acres
$869,000
Pending
7 Laurie Lane South Salem, New York
3 Beds 4 Baths 2,576 SqFt 2.11 Acres
$849,000
Pending
2 Hastings Court South Salem, New York
4 Beds 3 Baths 2,513 SqFt 1.9 Acres
$829,000
Active
8 West Lane South Salem, New York
3 Beds 2 Baths 1,852 SqFt 1.94 Acres
$789,900
Active
98 Smith Ridge Road South Salem, New York
4 Beds 3 Baths 2,450 SqFt 2.01 Acres
$779,000
Pending
14 Howe Street South Salem, New York
3 Beds 3 Baths 2,490 SqFt 0.7 Acres
$749,000
Active
24 Benedict Road South Salem, New York
4 Beds 2 Baths 1,846 SqFt 2 Acres
$749,000
Active
48 Sabbath Day Hill Road South Salem, New York
4 Beds 3 Baths 3,100 SqFt 2.01 Acres
$710,000
Active
17 Kingswood Way South Salem, New York
3 Beds 2 Baths 1,690 SqFt 1 Acres
$699,000
Active
25 Twin Lakes Road South Salem, New York
4 Beds 3 Baths 1,944 SqFt 0.543 Acres
$650,000
Active
59 Grandview Road South Salem, New York
3 Beds 2 Baths 1,360 SqFt
$649,000
Active
12 Truesdale Lake Drive South Salem, New York
4 Beds 2 Baths 1,875 SqFt 0.5 Acres
$495,000
Coming Soon
242 Deer Hill South Salem, New York
2 Beds 2 Baths 1,300 SqFt 0.016 Acres
$425,000
Active
3 Lake Avenue South Salem, New York
2 Beds 1 Baths 872 SqFt 0.223 Acres
$425,000
Pending
73 Fox Run Road South Salem, New York
2 Beds 2 Baths 1,070 SqFt 0.016 Acres
$415,000
Pending
110 East Street South Salem, New York
2 Beds 1 Baths 1,482 SqFt 0.73 Acres
$380,000
Active
6 Hemlock Road South Salem, New York
3 Beds 1 Baths 1,400 SqFt 0.26 Acres